(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

Base Information

• Chemical Name: (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione
• CAS No.: 85785-76-8
• Molecular Formula: C₂₄H₃₄Cl₂O₄
• Molecular Weight: 457.438
• Mol file: 85785-76-8.mol

Synonyms:(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

Chemical Property of (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

There total 43 articles about (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.1%

(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene (85912-78-3) → (2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione (85785-76-8)

Guidance literature:

With N-chloro-succinimide; calcium carbonate; In water; N,N-dimethyl-formamide; for 12h; Ambient temperature; 1) deoxygenation;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield: 43.4%

(+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene (85912-78-3) → (+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione (85785-76-8)

Guidance literature:

With N-chloro-succinimide; calcium carbonate; In water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(82)80152-4

Reference yield:

3-methylpent-2-en-4-yn-1-ol (6153-06-6,105-29-3) → (+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione (85785-76-8)

Guidance literature:

Multi-step reaction with 12 steps

1: p-TsOH_.H₂O / diethyl ether / 0 - 25 °C

3: 1.7 g / NaH / benzene / 2 h / 10 °C

4: 1.) LiNPr₂; 2.) HMPA / 1.) THF, -20 deg C, 20 min; 2.) -20 deg C, 1.5 h

5: 1.0 g / 2percent NaOH / H₂O / 4 h / Heating

6: 98.6 percent / acetic acid; tetrahydrofuran; H₂O / 3 h / 40 - 50 °C

7: 87.7 percent / pyridine / Ambient temperature

8: 86.3 percent / MeOH,anhydrous p-TsOH / benzene / 96 h / Ambient temperature

9: 64 percent / K₂CO₃ / methanol; H₂O / Ambient temperature

10: 1.) n-BuLi, p-TsCl; 2.) LiBr / 1.) n-hexane, ether, HMPA, 0 deg C, 20 min; 2.) n-hexane, ether, RT, overnight

12: 43.4 percent / CaCO₃, NCS / dimethylformamide; H₂O / Ambient temperature

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; N-chloro-succinimide; n-butyllithium; lithium di-n-propylamide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; calcium carbonate; lithium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)96890-5

upstream raw materials:

(+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene

(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene

(+/-)-(2'Z,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene

3-methylpent-2-en-4-yn-1-ol

Downstream raw materials:

(+/-)-(2'E,4'E)-4-chloro-2-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol

3-Chloro-4,6-dihydroxy-2-methyl-5-[(2Z,4E)-3-methyl-5-((1S,2S,6S)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde

(+/-) ascochlorin

3-chloro-4,6-dihydroxy-2-methyl-5-decane)-2,4-pentadienyl>benzaldehyde